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相关概念视频

Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

4.0K
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
4.0K
Preparation of Amides01:29

Preparation of Amides

3.2K
Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
3.2K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.3K
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
3.3K
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

3.6K
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
3.6K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

1.9K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
1.9K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

3.5K
The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
3.5K

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伊米达索皮里丁胺基:合成,

Rana Abdelaziz1, Justin M Di Trani2, Henok Sahile3

  • 1Institut Für Pharmazie, Martin-Luther-Universität Halle-Wittenberg, Halle (Saale) 06120, Germany.

ACS omega
|June 5, 2023
PubMed
概括

Q203是一种伊米达索皮里丁胺基 (IPA),向菌根细菌的电子运输链. 研究人员合成了27种类似物,以了解IPA的机制,发现菌根菌对人类线粒体具有选择性.

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科学领域:

  • 生物化学 生物化学
  • 药用化学 医学化学
  • 微生物学 微生物学

背景情况:

  • Q203 (telacebec) 是一种伊米达索皮里丁胺 (IPA) 胺基,可以抑制真菌菌呼吸道CIII2CIV2超复合体.
  • 了解IPAs的分子作用机制对于开发新的抗菌素剂至关重要.

研究的目的:

  • 综合和评估27种新型IPA类似物,以检测它们对菌根细菌电子运输链 (ETC) 的抑制活性.
  • 研究这些化合物的结构-活性关系 (SAR).
  • 与线粒体ETC相比,评估IPAs对菌根ETC的选择性.

主要方法:

  • 采用七步合成方案,制备了27种IPA类似物.
  • 氧气消耗测定用于确定化合物对纯化Mycobacterium smegmatis CIII2CIV2.2.的抑制作用.
  • 在实验室中进行了针对Mycobacterium tuberculosis的生长抑制试验.

主要成果:

  • 对Q203和对M. smegmatis CIII2CIV2的化合物27的IC50值分别为99 ± 32nM和441 ± 138nM.
  • 所有合成的IPAs,包括Q203,通过不抑制线粒体ETC.表现出选择性.
  • 在体外CIII2CIV2抑制和Mycobacterium结核病增长抑制之间没有观察到完美的相关性.

结论:

  • 合成的IPA类似物通常支持由Q203结合的M. smegmatis CIII2CIV2结构衍生的SAR.
  • 观察到CIII2CIV2抑制与细胞活性之间缺乏完美的相关性,这表明菌根菌中存在潜在的耐药性机制.
  • 对菌根细菌耐药机制的进一步研究是有必要的,以充分阐明这些化合物的活性.